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Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Overview

The Wicked St. Augustine tour delves into the unwritten history of the nation's oldest city. You will hear stories of the illicit industries that made the town a financial success, all while avoiding the reputation of a sinful city. From its founding St. Augustine had a thriving tavern, gambling and prostitution industry, even while portraying a city founded on religious principles. See the locations of high stakes gambling, speak easy taverns, and private clubs which skirted around the laws of the day, like prohibition. Learn how the political powers knew of these activities, secretly supported their providers, all while keeping a squeaky clean image.

City: St Augustine

Wed 02 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Wed 02 Jul

Starting at $30.00

Make a reservation

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What's Included

Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'

Additional Info

Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Suitable for all physical fitness levels

What To Expect

Lightner Museum

The courtyard in front of the old Alcazar Hotel, now the Lightner Museum, also in full view of the old Ponce de Leon Hotel, now Flagler College.

Historic Tours of Flagler College

Location of the old Ponce de Leon Hotel, built by Henry Flagler. This was the epitome of luxury and decadence during the Gilded Age.

St. George Street

Here the stories of the private clubs that lined this and the adjoining streets, gambling halls, speak easies, and boarding houses for upscale vacationers, to the working men of the city.

Plaza de la Constitucion

From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).

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Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (81)

Amanda_S

Jun 2024

Very informative and fun! Ann will take as long as you want and give you as much history as you wish. She’s a great storyteller. You get to hear the history you wont hear about anywhere else. Highly recommend!

Response from Host

Jun 2024

Ann is a great storyteller, agreed. We are so glad you enjoyed the experience. Have a wonderful time exploring our city.

ASeidl105

May 2024

Ann was fascinating and her inside knowledge of the workings of St. Augustine society was extensive to say the least. Her descriptions of events and the people involved in them was colorful and really brought her stories to life.

Response from Host

May 2024

Ann is a talented and passionate storyteller. Thank you so much for the kind words and exploring the hidden side of our city's history.

Meechelle_P

Apr 2024

It was a great experience. Ann had so much knowledge of the area and had done extensive research. The one note, she has so much to share and is so passionate about the history of St. Augustine, she can't do the tour in an hour and a half....it will go longer so be prepared, but well worth it.

Response from Host

Apr 2024

Yes, Ann is very passionate about her subject matter. She does run long, but always entertaining. Have a great time visiting.